Chemoenzymatic synthesis of genetically-encoded multivalent liquid N-glycan arrays

Chih-Lan Lin, Mirat Sojitra, Eric J. Carpenter, Ellen S. Hayhoe, Susmita Sarkar, Elizabeth A. Volker, Chao Wang, Duong T. Bui, Loretta Yang, John S. Klassen, Peng Wu, Matthew S. Macauley, Todd L. Lowary and Ratmir Derda ()
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Chih-Lan Lin: University of Alberta
Mirat Sojitra: University of Alberta
Eric J. Carpenter: University of Alberta
Ellen S. Hayhoe: University of Alberta
Susmita Sarkar: University of Alberta
Elizabeth A. Volker: University of Alberta
Chao Wang: The Scripps Research Institute
Duong T. Bui: University of Alberta
Loretta Yang: Lectenz Bio
John S. Klassen: University of Alberta
Peng Wu: The Scripps Research Institute
Matthew S. Macauley: University of Alberta
Todd L. Lowary: University of Alberta
Ratmir Derda: University of Alberta

Nature Communications, 2023, vol. 14, issue 1, 1-15

Abstract: Abstract Cellular glycosylation is characterized by chemical complexity and heterogeneity, which is challenging to reproduce synthetically. Here we show chemoenzymatic synthesis on phage to produce a genetically-encoded liquid glycan array (LiGA) of complex type N-glycans. Implementing the approach involved by ligating an azide-containing sialylglycosyl-asparagine to phage functionalized with 50–1000 copies of dibenzocyclooctyne. The resulting intermediate can be trimmed by glycosidases and extended by glycosyltransferases yielding a phage library with different N-glycans. Post-reaction analysis by MALDI-TOF MS allows rigorous characterization of N-glycan structure and mean density, which are both encoded in the phage DNA. Use of this LiGA with fifteen glycan-binding proteins, including CD22 or DC-SIGN on cells, reveals optimal structure/density combinations for recognition. Injection of the LiGA into mice identifies glycoconjugates with structures and avidity necessary for enrichment in specific organs. This work provides a quantitative evaluation of the interaction of complex N-glycans with GBPs in vitro and in vivo.

Date: 2023
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DOI: 10.1038/s41467-023-40900-y

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